


Squeeze Me Baby

by BabysNotaProp (SuzetteB)



Category: Supernatural
Genre: F/M, Fluff and Smut, Matchmaker Sam Winchester, Rare Pairings, Tumblr Prompt, Vaginal Fingering, Vaginal Sex, writing challenge
Language: English
Status: Completed
Published: 2018-10-10
Updated: 2018-10-10
Packaged: 2019-07-29 06:53:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,542
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16258952
Author URL: https://archiveofourown.org/users/SuzetteB/pseuds/BabysNotaProp
Summary: Dean skeptically agrees to a blind date his matchmaking brother arranges, but he would've never guessed the person Sam set him up with. Has love been right under Dean's nose ever since their days of pishtacos and sharing powdered donuts?





	Squeeze Me Baby

**Author's Note:**

> Written for roxyspearing's 1k giftastic challenge! Hopefully the gif works. If not, just use your imagination. *wiggles fingers*
> 
> Anyone who's familiar with my work knows I usually write either Destiel or character x reader. This is new territory for me, especially as a rarepair, so we'll see how it goes over! Enjoy :)

“Come on Sam,” Dean pressed as his brother held the steering wheel. “You can’t just set up dates for me. What if this chick is ugly?”

 

“She’s not,” Sam insisted, a smirk tugging at his cheeks. “Would you just calm down and let me drive?”

 

Sam had been driving for hours. Dean hadn’t tried to stop him from driving. Sam needed to stop being a little bitch. 

 

“Look, will you tell me something? Anything,” Dean begged. “Did you find her on a dating app?”

 

“Not telling.”

 

“Is that a yes?”

 

Sam shook his head defiantly. “We’re almost there.”

 

“Just ‘cause she looked a certain way online, doesn’t mean it’s real life. She could be some seventy year old hippie!”

 

Sam couldn’t stop the soft chuckle. “Okay, I didn’t find her on the internet. I’ll tell you that much, since we’re almost there.”

 

“You know I can get myself laid just fine?”

 

“This isn’t about that, you jerk,” Sam said with an eyeroll. “You’re going to want to see this one again. I promise.”

 

“What, do you know her personally or something?”

 

Sam said nothing in response and instead kept his eyes trained on the road.

 

“Oh my god,” Dean mumbled, “am I getting sloppy seconds from you?”

 

“Dean! No,” Sam yelled, startling his brother. “Shut up, okay? You sound like a lunatic.”

 

“You’re a lunatic, you… lunatic,” Dean whined back, at his wits end for comebacks. His head was getting fuzzy as the nerves ate at him. Why did Sam think it was okay to set him up on a blind date? And why was he being so effin’ cryptic?

 

In the seeming middle of nowhere, Sam rolled the Impala into a park-and-ride and cut the engine. Dean looked around nervously, and Sam glanced over at him with a twinkle in his eye. Out of his peripheral vision, Dean noticed someone hop onto their truck caps and a breath got caught in his throat as his eyes wandered up.

 

 

“Hey Sammy, it’s Donna,” Dean noted excitedly. He looked at Sam’s face and saw the twinkle. 

 

Oh.

 

“Wait,” Dean gasped. “You set me up with Donna Hanscum?”

 

Sam laughed victoriously. “Dean, I can’t believe you haven’t asked her out already. She’s a great lady, and you two get along. Now get outta here.”

 

Not listening to Sam’s parting words, Dean got out of the car and shut the door behind him. He didn’t notice Sam back up and leave him. With butterflies in his stomach, Dean met Donna’s gaze as he swallowed and walked up to her. She was adorable as ever, with her boots and coat and hair and… Dean remembered to breathe as he realized he had seen her multiple times, all knowing these endearing things about her, but not letting himself pursue them. Why hadn’t he pursued them? He felt like an idiot.

 

“Hiya, Dean!” she greeted with a grin. 

 

“Uh,” Dean stammered as they embraced. “Hey Donna. Sam wouldn’t tell me anything, and I saw you, and I uh…” He couldn’t stop smiling. She was so warm and nice and smelled good. “I can’t believe we haven’t given this a shot already.”

 

“I know, right?” she agreed as they broke the hug. “Well, where to?”

 

Breathe, Dean. Breathe. It’s just Donna. “Wanna grab something to eat?” 

 

“You betcha,” she replied before climbing back into her truck. Dean followed into the passenger seat and settled in, trying to take in this whole scenario. He was on a date. With Donna. Light-up-the-room with her smile, laugh-til-your-sides hurt, Donna. She made him so happy every time they reunited. She already knew him, and he already knew her, and the more he thought about how much sense they made, the less inhibited he was about the date. 

 

Sam had brought up the possibility of Dean finding someone else in the life. Someone who understands the nuances of being a hunter. He just never expected that person to already be in his life. Maybe he never allowed himself to go there because he was afraid of causing more pain. One thing was for sure, Donna had known her share of pain as well, so whatever this life could dish out, he had already seen her handle it. His heart swelled with hope. This could work.

 

They decided on a quaint mom-and-pop restaurant Donna knew of, and dinner flew by with stories of happenings since their last meeting. Dean didn’t know what sorts of things people talked about on a first date, but Donna seemed more comfortable with it, so he took queues from her on where topics led. So far they had discussed Jack, Sam almost burning down the bunker with a kitchen fire, his childhood trauma that made him hate small spaces, and everything Donna had been up to. She was staying busy with work, but had fit in some hunts when the monsters wandered too close to home.

 

Once again in Donna’s truck, the two named off ideas of what to do next. The night was still young and the town was brimming with interesting things to do. Dean inhaled the normalcy like a breath of fresh air. It all seemed so civilian. He wasn’t used to it. Not that he didn’t enjoy it, but… he kind of wanted to shake things up a bit.

 

“Let’s work a case,” he suggested with a cheeky grin.

 

“What?” Donna laughed. “Are you serious?”

 

“Yeah, why not!”

 

Donna nodded her head for a moment, then turned the key in the ignition. “I know where there’s a vamp nest.”

 

“You got some machetes?”

 

Donna leered at him with a sassy glint in her eye. “You know I do, Dean Winchester.”

 

The hunt was short and messy, but Dean and Donna walked away with bloody machetes and more vampire puns than was necessary. As they caught their breath and buckled up, Dean glanced over and took in the sight of Donna with renewed vision. She had a leaf in her hair, a smear of dirt on her cheek, smudged mascara and she was… beautiful. She was strong, brave, and fun to be around. Her smile was just… wow. Her lips. 

 

“Dean?” Her voice tore his eyes back to hers. “You wanna get dessert? Maps shows this frozen custard place is still open.” She held up her phone, not wanting to point out his lingering stare.

 

“Yeah,” he agreed lightly. A warm feeling pooled in his gut. All he could think about were her lips. He wanted to kiss her. The thought of his mouth on hers sent a jolt right between his legs. Nevermind. He wanted to do more than kiss her. Was that normal for a first date? Oh god, he was probably overstepping.

 

They sat at a table beside the stand-alone custard joint, other people in line and wandering off to the other side. She had a sundae. He had a dipped cone. Dean had no idea what they were talking about, but he was having the absolute time of his life and Donna was so damn  _ funny _ . She could be serious when the need arose, of course, but in this context, it was nice to have someone so easy to talk to.

 

On her last bite, Dean noticed a small drip of fudge on her lip. Not thinking, he swiped it off with his thumb and panicked as he smothered it on his jeans. She was looking at him with wide eyes, but void of any disgust or shock. What did that face mean? Was this a normal first date face? Her lips looked soft. Oh god.

 

“Can I… uh…?” he began asking in a broken sentence.

 

“Uh huh,” she answered with a short nod.

 

Relief washing over him, Dean leaned over and pressed his lips on hers. He was terrified of it feeling wrong, of her pulling back, of waking up to find it a dream, but those things never happened. It wasn’t a dream. It felt more right than anything else so far. And instead of pulling back, she nudged forward and deepened the kiss.

 

The next few minutes were a blur, but during them Dean came to the realization that 1) he had major hots for Donna Hanscum and 2) she was just as into it as he was. He was definitely kicking himself for not doing this sooner. Not long after leaving the custard place but not soon enough for their taste, they kicked the hotel room door shut, lips still locked. Dean pinned her to the door, lifting her enough for her legs to wrap around him. He grinded against her with a grunt, desire rapidly building in him.

 

“I don’t usually do this,” he explained between kisses.

 

“What? Sleep with someone on the first date?”

 

“No,” he clarified. “I mean I don’t usually date. I don’t know if I’m moving too fast or what.”

 

“Oh honey,” she cooed. “You’re moving just right.”

 

With a growl, Dean set her down and placed open-mouthed kisses on her neck. She arched into the touch, leaning her head back and slipping her fingers under his shirt. Encouraged by the touch, Dean slipped off her coat and ran his fingers down her buttons, popping them open one by one. He got an eyeful as her breasts heaved over her camisole.

 

“Oh god,” Dean muttered between shallow breaths. “Shit, Donna. You’re gorgeous.”

 

Pink rising to her cheeks, Donna grabbed Dean’s face and kissed him hard while feeling the dip of his hips and roll of abs from reaching under his clothes.

 

Dean came up from the kiss with a wild look in his eye. “Don’t be shy,” he chuckled darkly as he slipped off his t-shirt. 

 

“Jesus, Mary and Joseph,” Donna whispered as she beheld his beautiful torso. She knew Dean was fit, but… damn. He was so much more perfect than she imagined. After throwing off her camisole, she wrapped her hands around him and felt the rise and fall of his back muscles as arousal pooled in her panties.

 

Dean slipped his fingers under her bra straps, kissing her skin as he uncovered it. Unhooking it, he searched her face for apprehension before dropping her bra to the floor. Her breasts bounced with the absence of support, wind knocked out of him as her nipples hardened in the cold room.

 

Backing her up as he kissed her, he lifted her slightly at the edge of the bed and lowered her down. He wasn’t exactly sure what he had done to deserve someone so stunning and right for him and  _ good _ , but he thanked every deity he could name and accepted it. He kissed between her breasts and she hummed happily before taking one of his nipples in her fingers, to which his knees buckled and he let out a breathy moan.

 

Tearing the rest of their clothes off, they explored each other, touching and squeezing, never in a hurry. Donna’s core pulsed with need when Dean sucked on the underside of her breasts and laid her on her stomach to kiss her back. She took him by surprise when she flipped him onto his back and straddled him, running her mouth over every inch of his stomach and chest, working higher until she reached his jaw and her wet pussy dragged her arousal across his lower abdomen.

 

Feeling the wetness meeting the cool air on his skin, he trailed his fingers to her inner thighs and dipped a finger into her entrance.

 

“Fuck, Donna,” Dean mumbled. She huffed a breath when he added a second finger and began pumping in and out of her. “You like that, baby?” He was unsure of the appropriateness of pet names, but she smiled in response. “You’re so fucking beautiful, Donna. Shit, I never want this to end.”

 

Donna reached behind her to curl her fingers around his thick cock. “Fuck me, Dean,” she said. “I need you.”

 

Sitting up, Dean pushed Donna back down and hovered over her, hands tracing her soft, smooth stomach, hips, thighs. He placed a kiss right below her belly button, to which she giggled, and he smirked as he held his cock to her ready entrance. 

 

“You ready, babe?” he murmured. She nodded. Filling her up in one slow, fluid motion, Dean watched her pussy swallow his length inch by inch. He let out a long moan after bottoming out, cock squeezed pleasantly by her walls. As he began to move inside her, she squirmed under him, meeting every thrust. Moving together in perfect harmony, he filled her over and over at a steady but relaxed pace, until his cock began to grow tingly and the throbbing need for release sent him snapping in and out of her hungrily. 

 

She was moaning beneath him, face flush and voice arousing. He raised her legs and held them over his shoulders as he plunged deeper into her, a proud smile gracing his face as the new angle brushed her g-spot and sent her screaming.

 

“You gonna come for me, Donna?” Dean huffed in between thrusts, beads of sweat starting to form on his brow. “Huh baby?” Letting go of one leg, he took her clit between his index and middle finger and gently tugged, slick from her entrance making her glide right through his fingers. He repeated the motion, eliciting a moan on every pass, and watched her face as she threw her head back in orgasm.

 

It was the most beautiful thing Dean had ever seen. Her mouth wide open, his name on her lips, body convulsing under the waves of her coming hard enough to see stars. He looked on as she came down from her high, and then he dropped her other leg and chased his own end. He rammed into her so hard, her head bumped against the headboard, but she was laughing with delight. In two final lunges, Dean’s eyes rolled back and he came inside her. He kept panting and pushing until every drop of his seed had painted her walls and came oozing out, then he lowered himself onto her and rested his head in the crook of her neck.

 

They stayed like that until they could catch their breath. 

 

“Wow,” Dean groaned. He pulled his softening cock out of her and laid beside her on the bed. This had been the most incredible night of his life. And when the realization hit him that it wasn’t over yet, he couldn’t help but smile. This is where one night stands would either conk out beside him or high-tail it out of there. But Donna wasn’t getting up or turning away. 

 

“Yeah,” she smiled broadly. “Wow is right. Where the hell have you been, anyway?”

 

Dean leaned in and kissed her nose.

 

The next day, Sam finally got a text from Dean. So the night went well, after all. Sam sighed with relief and made his way back to the park-and-ride, where Dean and Donna were waiting in the truck comparing pistols and blaring the radio. Dean didn’t say anything the entire ride home, but that was fine. His permanent smile said everything.

 

Once back at the bunker, Dean’s phone pinged and he looked down to see a text from Donna:

 

_ 2nd date next Friday okay? ;) _


End file.
